President Obama will make a campaign swing through Boston on Monday for a series of fundraisers

WASHINGTON – President Obama will make his first trip of the year to Massachusetts on Monday when he appears in Boston for a fundraising triple-header – critical events that his top local bundlers are counting on to add millions to his campaign coffers.

Obama will first attend an intimate campaign roundtable at Hamersley’s Bistro in the South End with 25 supporters who paid $40,000 each to attend, said a campaign official. The afternoon gathering will be hosted by Boston advertising magnate Jack Connors, who last spring held a $17,900-a-head dinner at his Brookline home for the president.

Then, according to a Boston fundraiser, around 4:30 p.m. Obama will move onto Symphony Hall, where he will speak to a crowd of 1,800 people after first posing for photos with the host committee. General admission tickets for the large fundraiser start at $250, but a limited number of Gen44 tickets, for younger Obama supporters, went for $144.

Advertisement - Continue Reading Below

He will wrap up the fundraising swing through town with a $17,900-a-head dinner for 100 people at the Weston home of Judi and Douglas Krupp, philanthropists with a family-run charitable foundation. Douglas Krupp is the co-founder of the Berkshire Group, a Boston-based real estate investment company. His brother, George, a Berkshire co-founder and CEO, is a bundler for Obama.

Proceeds from the evening’s events will go to the Obama Victory Fund, a joint fundraising committee of Obama for America, the Democratic National Committee and several state Democratic parties.

The Globe reported last month that donor exuberance for Obama in the Bay State has waned since the heady days of 2008, with the number of Massachusetts supporters contributing the maximum to the president’s campaign fund plunging nearly 50 percent compared to the same time period during his fledgling run.

Key bundlers said the reasons were varied – a natural decline in enthusiasm from the frenzy of Obama’s first bid after the realities of governance set in, combined with a down economy hitting donors’ pocketbooks and heated congressional races competing for cash. But all hoped to make up for the loss with Monday’s series of fundraisers.

Obama’s trip to Boston comes just before the quarter ends, following news that in May, for the first time, Mitt Romney’s joint fund-raising committee outraised the incumbent’s. Romney raked in $76.8 million, compared to Obama’s $60 million.

While Obama will be campaigning Monday on Romney’s home turf, the state remains a Democratic stronghold. Obama has raised $5.5 million in the state compared to Romney’s $4.4 million so far this election cycle, according to the Center for Responsive Politics.

Earlier on Monday Obama will speak at Oyster River High School in Durham, N.H. The public can pick up free tickets at any of the Obama campaign offices in the state starting at 9 a.m. Friday.

Tracy Jan can be reached at tjan@globe.com. Follow her on Twitter @GlobeTracyJan.